Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
DETAILED ACTION
Claims 1, 10 and 12-14 are pending in the application. Claims 1, 10 and 12-14 are rejected.
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on August 25th, 2025 has been entered.
Response to Amendment / Argument
The claim amendment filed August 25th, 2025 contains two instances of claim 11, and claims 12-14 (labeled as previously presented and original) have been renumbered as claims 11-13. This claim numbering is not in accordance with 37 CFR 1.126. The second instance of claim 11 and claims 12-15 having been renumbered as claims 12-16.
On page 4 of the response, Applicant traverses the rejection of claims 9 and 10 under 35 USC 112(b) on the grounds that “Claims 9-10 have been canceled…”. Since claim 10 is still pending, the rejection is maintained over claim 10.
On page 4 of the response filed August 25th, 2025, Applicant begins traversing the rejection under 35 USC 103. Applicant’s amendments have necessitated changes to the previously presented rejection; however, Applicant’s remarks will be addressed as they relate to the rejection below.
Applicant discusses retrofitting and refers to alleged extensive experimental work such that “the plant is in communication with a polymerization plant via a conveying belt.” This is limitation is not recited in the instant claims. Furthermore, it is not related to the amendment to claim 1 where the oxidation zone is retrofitted. Regardless, defining equipment as being retrofitted is still considered a product-by-process since it is a limitation that defines an object based on how it was generated.
On page 5 of the response, Applicant asserts “if the examiner’s assertions are correct then it would not be possible in the future to have any plant that is integrated to be found patentable.” The instant claims being obvious is consequence of the lack of any defining limitations regarding how integration occurs. Currently the only limitations involve proximity, which is addressed in the rejection. As noted above, Applicant simultaneously argues that extensive experimentation occurred to result in the use of a conveying belt, but this limitation is not found in the instant claims. Applicant further states “catalyst recovery and mother liquor recovery are also integrated into the plant making a total of three plants, FDCA, polymerization, and catalyst recovery or purge plant that are integrated.” The claims only require one plant to be present as discussed in the rejection.
For these reasons, Applicant’s arguments are not found persuasive regarding the 103 rejection below, which has been modified as necessitated by Applicant’s amendments.
Claim Objections
The word “and+” in claim 1 should be replaced with “and”.
Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 10 recites the limitation "said carboxylic acid composition" in lines 1 and 2. There is insufficient antecedent basis for this limitation in the claim. Claim 1 has been amended to delete reference to a “carboxylic acid composition”.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 1, 10 and 12-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over U.S. Patent PGPub No. 2012/0302769 A1 by Janka et al. in view of U.S. Patent PGPub No. 2015/0321119 A1 by Parker et al. and in further view of Ketel, C. EPCA, The Role of Clusters in the Chemical Industry, 2007, pages 1-55 and in further view of Port of Antwerp, Investment Guide, April 2015, pages 1-34 and in further view of U.S. Patent No. 7,863,407 by DeBruin et al.
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
Janka et al. teach the following general method on page 1:
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FDCA meets the limitation of instant claims 9 and 10 as the product of step (a). The starting material in the prior art is Applicant’s instant elected species of an oxidizable compound. The prior art teaches the use of a solvent, oxygen (an oxidizing gas) and a catalyst system along with a temperature that largely overlaps with the range of instant claims 1 and 12. Regarding the catalyst limitations of step (a), Janka et al. teach the following on page 4:
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The catalyst amounts largely overlap with the ranges instantly claimed. Furthermore, the examples found in Tables 1-3 on page 10 for the catalyst each fall within the scope of the instant claims of 2000 or 2500 ppm Co, between 93.5 and 116.8 ppm Mn and between 2500 and 3000 ppm Br. The same ranges apply to the catalysts of Table 5 on page 12. The prior art further teaches the following embodiment on page 17:
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The ranges above are within the scope instantly claimed. Regarding the limitations of claim 1 regarding a yield of “up to 89.4%” and a “b* less than 6;” Janka et al. teach the following on page 5:
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Similarly, Janka et al. teach the following on page 8:
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The instantly claimed yields and b* overlap with the ranges taught in the prior art. Furthermore, the solvent used in the reaction would meet the limitation of “an oxidation solvent” being produced.
Regarding the limitation of “said furandicarboxylic acid is dried,” in step (b) of claim 1, Janka et al. teach the use of a drying zone in Figure 1 and, for instance, paragraph [0006] on page 1.
Regarding the limitation of a purge zone and routing of claim 1, Janka et al. teach the following diagram in Figure 1:
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.
Accordingly, Janka et al. teach the use of a purge zone.
Ascertainment of the differences between the prior art and the claims. (See MPEP § 2141.02)
The prior art does not teach a step where a portion of mother liquor stream is routed to an oxidation zone.
The prior art does not teach performing polymerizing within 1 mile as recited in instant step (b) and that polymerization is conducted in a PET production plant.
Additional limitations are addressed below.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2141.02)
Regarding instant limitation “wherein a portion of mother liquor stream is routed…”, the reference by Janka et al. corresponds to Application Serial No. 13/228,799. Parker et al. teach the following on page 1 (paragraph [0003]):
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Accordingly, the disclosure of Parker et al. appears to be an extension or improvement on the disclosure and method of Janka et al. Parker et al. discuss a method for recovering different portions in a method of making FDCA. Regarding particular steps, Parker et al. teach the following:
[0004] Disclosed is a method for recovering a portion of oxidation solvent, a portion of oxidation catalyst, and removing a portion of oxidation by-products and raw material impurities from a solvent stream generated in a process to make furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing a feed stream comprising at least one oxidizable compound selected from the following group: 5-(hydroxymethyl)furfural (5-HMF), […] to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) in an oxidation zone, cooling a crude carboxylic acid slurry in a cooling zone to generate a cooled crude carboxylic acid slurry, removing impurities from a cooled crude carboxylic acid slurry in a solid-liquid separation zone to form a low impurity carboxylic acid stream and a mother liquor stream, routing at least a portion of the mother liquor stream to a mother liquor purge zone to generate a recycle oxidation solvent stream, a recycle catalyst rich stream, a raffinate stream, and an impurity rich waste stream.
A person having ordinary skill in the art in seeking to develop an overall approach based on Janka et al. would have been motivated to incorporate the recovery steps of Parker et al. to be able to avoid wasting solvent, catalyst, etc. including recycling catalyst.
Regarding instant step (b), Janka et al. teach in paragraph [0005] that the material being generated (FDCA) is useful in the preparation of polymers. In the interest of extending the prior art method to generate useful materials such as the polymers explicitly taught by Janka et al., a person having ordinary skill in the art would have been motivated to polymerize the material obtained in instant step (a).
Regarding the limitation of having polymerization and purge zone within 1 mile, a person having ordinary skill in the art would have at least been motivated to perform these reactions in close proximity in order to minimize the cost associated with transporting the product of step (a). Furthermore, a person having ordinary skill in the art would have been familiar with the use of chemical plant clusters. Ketel teaches the following on page 20:
The chemical industry uses many input factors and produces many outputs that are bulky and costly to transport. In addition, the geographical location of key feedstock inputs, predominantly oil and natural gas, do not match with the location of key markets for chemical products. Transportation costs are a significant part of overall costs along the value chain. This creates an environment where companies across different stages of the respective production process naturally co-locate to minimize on transportation costs throughout the industry value chain. It creates an environment, where clusters emerge naturally at locations with good transportation infrastructure. And it creates an environment where the presence of specialized logistical companies and proximity to related transportation and logistics clusters provide clear benefits.
A person having ordinary skill in the art would have additionally been familiar with plants located within 1 mile of each other. For instance, Port of Antwerp teaches the following on page 2:
[…] With this investment guide we seek to support your decision-making process. The Port of Antwerp is home to the largest integrated oil and chemical cluster in Europe. Here you will find all the necessary partners for your enterprise: suppliers of raw materials and intermediates, technical contractors and logistical support, financial, legal and administrative services, and of course… customers. […]
A map is provided on page 11 where adjacent plants are located within 1 mile of each other. For instance, the top grouping of five plants on page 11 are each within a mile of each other. A person having ordinary skill in the art would have been familiar with the development of chemical plants in close proximity and would have been motivated to perform the steps discussed above within a cluster to lower transportation costs.
Besides the use of a cluster of separate plants, the instant claims embrace embodiments where the plant producing FDCA, polymerizing plant and “PET production plant” are the same plant. Regardless, paragraphs [0004] and [0005] of Janka et al. teach that FDCA is useful as an alternative to terephthalic acid (TPA) and a person having ordinary skill in the art in switching from terephthalic acid to FDCA-based polymers would have been motivated to use the plant already in possession rather than purchasing or constructing a new facility. Furthermore, at least in the interest of optimizing the FDCA procedure, a person having ordinary skill in the art would been motivated to continue producing TPA/PET until the FDCA process could be reliably implemented.
Regarding the limitation of instant claim 1 of the oxidation zone at the end of step (a) being retrofitted, Janka et al. teach the use of an oxidation reactor and the instant limitation of “retrofitted” appears to be a type of product-by-process limitation within a method claim, i.e. where the limitation refers to previous manipulations of a particular physical component rather an active step requiring the previous terephthalic acid and/or isophthalic acid process. Regardless, paragraphs [0004] and [0005] of Janka et al. teach that FDCA is useful as an alternative to these two materials and a person having ordinary skill in the art in switching from terephthalic acid and/or isophthalic acid to FDCA-based polymers would have been motivated to use reactors already in possession rather than purchasing new reactors. The same rationale would apply to the limitation of step (b) “wherein said polymerizing is conducted in a PET production plant” since Janka et al. teach in paragraph [0004] “Aromatic dicarboxylic acids, such as terephthalic acid and isophthalic acid, are used to produce a variety of polyester products. Important examples of which are poly(ethylene terephthalate) and its copolymers.” Poly(ethylene terephthalate) is abbreviated as PET. Accordingly, a person having ordinary skill in the art in transitioning from terephthalic acid and related processes would have been motivated to repurpose facilities that were previously used for terephthalic acid including polymerization facilities that were used to generate poly(ethylene terephthalate). Furthermore, a person having ordinary skill in the art would been motivated to continue producing PET until the FDCA process could be reliably implemented.
Further regarding the use of TPA and PET plants and those in close proximity, a person having ordinary skill in the art would have been familiar with plants that have already been developed in close proximity where one plant performs oxidation to yield a dicarboxylic acid and the second produces polyesters thereof. For instance, DeBruin et al. claim the following general method in claim 1 (column 10):
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Furthermore, DeBruin et al. teach distances of less than 1 mile in column 2, line 44 as well as even lower distances in lines 48-53 of the same column.
Regarding instant claim 12, Janka et al. teach oxidation at these temperatures on page 18 as part of claims 7 and 8. Regarding instant claims 13 and 14, Janka et al. teach oxidation at these pressures on page 18 as part of claims 19 and 21.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MATTHEW P COUGHLIN whose telephone number is (571)270-1311. The examiner can normally be reached Monday - Friday, 10 am - 6 pm EST.
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/MATTHEW P COUGHLIN/Primary Examiner, Art Unit 1626